3,3'-Diaminobenzidine → benzobisimidazole Divinylene

HRID 1718

Reaction equation

HRID 1718 reaction equation
N[C:2]1C=C([C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[C:11]([NH2:16])[CH:10]=2)C=C[C:7]=1N.[C:17](O)(=O)/[CH:18]=C/C=C/C(O)=O>>[CH:2]#[CH:7].[CH:17]#[CH:18].[N:13]1[C:12]2[CH:14]=[CH:15][CH:9]=[CH:10][C:11]=2[NH:16][CH:17]=1.[N:13]1[C:12]2[CH:14]=[CH:15][CH:9]=[CH:10][C:11]=2[NH:16][CH:17]=1

Participants

3

Reactant 2

HCID 70713,3'-DiaminobenzidineHCID 5356793Muconic Acid

Product 1

HCID 86752219benzobisimidazole Divinylene

Procedure

3,3'-Diaminobenzidine (1.508 g, 7.04 mmol) was dehydrochlorinated with 83.3 wt % deaerated PPA in accordance with the procedure enumerated in Example 1. The product of this dehydrochlorination was reacted with trans,trans-muconic acid (1.0 g, 7.04 mmol) in accordance with the procedure of Example 1. This polymerization reaction was conducted for a total of 30 hours, the first 6 hours of which were at a temperature of 100° C. and the final 24 hours at 140° C. The product of this reaction was a yellowish-brown polymerization dope. This product was precipitated in water and purified by extraction, for 3 days, with water.

Workup

  1. customThis polymerization reaction
  2. customwas conducted for a total of 30 hours
  3. customthe first 6 hours of which
  4. customwere at a temperature of 100° C.
  5. custom24 hours
  6. customat 140° C
  7. customThis product was precipitated in water
  8. custompurified by extraction, for 3 days, with water

Sources & evidence

ORD record
ord-49f6270560624c5e98c775fdae86e129
Source dataset
uspto-grants-1998_03
Patent number
US05726282

Linked notes

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